Horse of a Winning Color

Under a clear blue sky on the first Saturday in May 1988, a large battleship-gray lady, ridden by the blue-and-gold-clad Gary Stevens collected the Kentucky Derby winner’s coveted blanket of red roses. Winning Colors, a tough and tenacious filly, made history by becoming only the third female to triumph in America’s most prestigious race, which was first run in 1875.

And while five females have started in the race in the past 28 years—including the ill-fated Eight Belles, who finished second in 2008 to winner Big Brown—a filly has not won the Derby since. The previous Derby-winning females were Regret in 1915 and Genuine Risk in 1980.

A daughter of prominent Irish-bred stallion Caro, also a gray, Winning Colors, who was foaled from the bay mare All Rainbows, was bred by Don and Shirley Sucher’s Echo Valley Farm near Georgetown. The filly was purchased for $575,000 by Thoroughbred trainer extraordinaire D. Wayne Lukas for businessman Eugene V. Klein at the 1986 Keeneland July yearling sale.

Heading to the track as a 2-year-old in the summer of 1987, Winning Colors captured her first-ever race at the venerable Saratoga Race Course in upstate New York. By late December, Stevens had become her regular jockey, guiding her to an impressive win in a Dec. 27 allowance race at Santa Anita Park in California, which would become her main stomping grounds leading up to the Derby.

“I had never experienced the kind of athleticism she showed me,” Stevens wrote in his 2003 book The Perfect Ride of his first race aboard Winning Colors. After that race, Stevens went back to the jockeys’ room and boasted to fellow rider Jacinto Vasquez, “I’m going to win the Kentucky Derby on that filly!” It was a prophetic statement.

The filly turned in stellar performances on the Derby trail that winter and early spring, including a win in the esteemed Santa Anita Oaks on March 13, which prompted Lukas to try her against males in the April 9 Santa Anita Derby, the prime Derby prep race on the West Coast.

Stevens shared Lukas’ confidence in Winning Colors’ ability to handle males. “Where this filly was concerned,” he wrote, “I had a strong gut feeling. I was sure she could face male competitors easily. For one thing, she was bigger than most of them, standing nearly seventeen hands tall [Editor’s note: Winning Colors actually was 16.3 hands—the equivalent of more than 5 feet, 5 inches at the ridge between the shoulder blades].

“For another,” he continued, “she was extremely focused, very professional when she raced, and she was tough. I could see that she intimidated other horses. I knew she could hold her own with the boys.”

Although it attracted the best 3-year-old runners in the West, the Santa Anita Derby was all Winning Colors.

“It wasn’t a problem,” Stevens wrote. “She won with little coaxing from me.”

With that encouraging victory, Winning Colors became Churchill Downs-bound. Lukas left his options open by entering his star filly in both the Kentucky Derby and Kentucky Oaks for 3-year-old fillies run the day before Derby Day. A Derby field can have as many as 20 starters, and Lukas wanted to be prepared to opt for the Oaks in case Winning Colors drew a difficult post position—one that could be detrimental to her performance in the crowded race. Both Lukas and Stevens were pleased when the filly ended up with post position 11.

Typically a front-runner in her races, Winning Colors quickly bounded to the head of the pack after the gates opened, commanding a 3-length lead at the first turn. She led the field easily throughout most of the 1 1/4- mile race, but Stevens sensed she was tiring in the last 50 yards.

“The last twenty-five seconds of the race were the longest twenty-five seconds of my life,” Stevens recounted. “We were alone until about five strides before the wire—that’s how fast Forty Niner was coming.” Forty Niner, trained by Woody Stephens and ridden by Pat Day, nearly caught Winning Colors, who held on by a neck for the win as well as a special place in Thoroughbred racing’s history books.

Winning Colors’ triumph was the first Kentucky Derby win for both Lukas and Stevens. Lukas went on to win three more Derbys (1995, ’96 and ’99), and Stevens won two more (1995, teaming up again with Lukas, and ’97).

Winning Colors gamely ran in the next two legs of the Triple Crown but was unable to duplicate her Derby-winning form. She finished a respectable third to winner Risen Star in the Preakness Stakes and a tired sixth in the 1-mile Belmont Stakes, also won by Risen Star.

Following a nearly three-month rest, Winning Colors was back on the track, and back to competing against females. She closed out 1988 with an appearance in the Breeders’ Cup Distaff at Churchill Downs in November. In what is considered by many as one of the most thrilling Thoroughbred races of all time, the undefeated mare Personal Ensign ran down Winning Colors in the stretch and defeated the Derby winner by a nose in the final stride.

Winning Colors triumphed in two races the following year and was retired with a record of eight wins from 19 starts and earnings of more than $1.5 million. Soon after her final race, in November 1989, Klein sold her to Gainesway Bloodstock Services, and she spent the remainder of her life at scenic Gainesway Farm near Lexington. She died on Feb. 17, 2008, at the age of 23.

As a broodmare, Winning Colors was never able to produce a foal that came close to herself in athletic ability. Although she was bred to some of the finest stallions, none of her 10 offspring became stakes winners.

“She didn’t get along with people and didn’t get along well with the other broodmares,” said Gainesway Farm Broodmare Manager Johnny Slugantz. She didn’t bully the other mares, but rather liked to stay by herself.

“She was her own girl. I think she knew she was special … She liked to be in charge. If you went to bring her in from the field, she would come, but only if she wanted to,” Slugantz said.

“She was a tough broodmare. And she was like that till the day she died.”

Certainly that toughness was a huge asset in Winning Colors’ athletic career—a career that included one of the most memorable Kentucky Derby triumphs of all time. Q